My reasoning is this, I'm in second to last place and my current summer job keeps me from keeping up, so I'm pretty much packaging those two together, so I can upgrade my keepers. Here is my team. Any other upgrades you think I can make?
C Carlos Santana (Cle - C,1B)DL 1B Eric Hosmer (KC - 1B) 2B Brandon Phillips (Cin - 2B) 3B Mike Moustakas (KC - 3B) SS Hanley Ramirez (Mia - 3B,SS) OF Matt Kemp (LAD - OF) OF Giancarlo Stanton (Mia - OF) OF Jason Heyward (Atl - OF) Util Nick Markakis (Bal - OF) Util Dexter Fowler (Col - OF) SP David Price (TB - SP) SP Johan Santana (NYM - SP) RP Jonathan Broxton (KC - RP) RP Dale Thayer (SD - RP) P Gio Gonzalez (Was - SP) P Addison Reed (CWS - RP) P Josh Beckett (Bos - SP) P Josh Johnson (Mia - SP) DL Carl Crawford (Bos - OF)DL BN Colby Lewis (Tex - SP) BN Jeremy Hellickson (TB - SP) BN Adam Wainwright (StL - SP) BN Matt Moore (TB - SP,RP) BN Roy Oswalt (Tex - SP)NA
If you're only planning to keep either HanRam or Tulo, and not the pitchers, I'd say make the trade. If you're planning to keep the pitcher as well, I wouldn't since Price is one of the top pitchers in baseball, who is still ascending.
If you're selling to get stud keepers, do a yardsale. Trade two of those young guys (hellickson and Phillips) for a Cano or Pedroia, and so on and so forth. Get 4 guys who were first round picks.
Sell out, or don't, but make a decision; if you stay somewhere in the middle you won't be any better off next year.
I think it comes down to who would be your 4th keeper. I would keep Kemp, Stanton, and either SS. The 4th spot would be between Santana, Hosmer, and Price if it were me. I agree that you could do a better deal to get your 4th keeper. Package Price and Phillips and go for Kershaw or Verlander. Or you could package Price and Hosmer/Santana for an upgrade.